The field of cascade polymer chemistry is expanding the traditional synthetic limits into the meso-macro-molecular frontier. Such polymers possess well-defined molecular topologies as they can be constructed in discrete layers rendering upon the molecule discrete, symmetric and consistent chemical characteristics.
These polymeric structures provide specific micellar molecules.
The synthesis and spectral features of cascade polymers, also referred to as arborols possessing two-, three- and four-directional microenvironments with functionalized polar outer surfaces, have been recently reported (1-8). Depending on their molecular shape, many of these macromolecules aggregate to form gels or show novel micellar characteristics in aqueous solution (3,7,8). In view of an interest in generating a spherical hydrophilic surface with a compact lipophilic core, the present invention provides a cascade system which in one embodiment emanates from a central adamantane core. This core includes bridgehead positions which have suitable geometry to mimic a tetrahedral nucleus and can be envisioned as an extended methane core. Such a core is an ideal starting point toward four-directional cascade polymers.
In constructing such spherical polymers, several further problems were uncovered. One such problem related to the generation of a tri-branched monomer which would not cyclize. More specifically, to provide tri-valent branching from a single branch of a polymer, at least two qualities are required. First, there must be directionality such that the monomer combines with the branch so as to expose three branch binding sites for further tiering of the macromolecule. The branches of the macromolecule extending from a central core must also extend sufficiently to be able to allow further reactions therewith for the additional tiering while not cyclizing onto themselves. Cyclizing removes branches from being chemically reactive thereby causing a dead-end to the tiering process. For example, the following reaction sequence generated the polymeric product set forth below.

Attempted oxidation of compound 11 by a RuO2 procedure of Irngartinger, et al. (9) resulted in limited success in that complete oxidation was not reproducible.
Applicant herein provides novel monomers which are ideal in that they do not cyclize and further can be used in a cascade system for producing macromolecular monomers through tetradirectional polymers, particularly on an adamantane, methane equivalent, or four-directional core.
Further, the present invention provides novel four-directional spherical dendritic macromolecules based on adamantane made in accordance with the novel method set forth herein.